WO2015176984A1 - Additif polyvalent pour préparation de revêtement de sol - Google Patents

Additif polyvalent pour préparation de revêtement de sol Download PDF

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Publication number
WO2015176984A1
WO2015176984A1 PCT/EP2015/060345 EP2015060345W WO2015176984A1 WO 2015176984 A1 WO2015176984 A1 WO 2015176984A1 EP 2015060345 W EP2015060345 W EP 2015060345W WO 2015176984 A1 WO2015176984 A1 WO 2015176984A1
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WO
WIPO (PCT)
Prior art keywords
formula
blends
alkyl
compounds
astm
Prior art date
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Ceased
Application number
PCT/EP2015/060345
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English (en)
Inventor
Luiz Antonio Martins Da SILVA
Juraci Marques Da Silva
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BASF SE
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BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
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Anticipated expiration legal-status Critical
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09G—POLISHING COMPOSITIONS; SKI WAXES
    • C09G1/00—Polishing compositions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • C09D5/024—Emulsion paints including aerosols characterised by the additives
    • C09D5/027—Dispersing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09G—POLISHING COMPOSITIONS; SKI WAXES
    • C09G1/00—Polishing compositions
    • C09G1/06—Other polishing compositions
    • C09G1/14—Other polishing compositions based on non-waxy substances
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09G—POLISHING COMPOSITIONS; SKI WAXES
    • C09G1/00—Polishing compositions
    • C09G1/06—Other polishing compositions
    • C09G1/14—Other polishing compositions based on non-waxy substances
    • C09G1/16—Other polishing compositions based on non-waxy substances on natural or synthetic resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09G—POLISHING COMPOSITIONS; SKI WAXES
    • C09G1/00—Polishing compositions
    • C09G1/06—Other polishing compositions
    • C09G1/14—Other polishing compositions based on non-waxy substances
    • C09G1/18—Other polishing compositions based on non-waxy substances on other substances

Definitions

  • Tributoxyethyl phosphate is a fire retardant but also a well known plasticizer and leveling agent with a reasonable performance in floor coating formulations.
  • tributoxyethyl phosphate contains phosphate, it is not welcome in terms of sustainability and eco-efficiency. Therefore, in the last years a lot of efforts have been done by the floor coating formulators to replace TBEP.
  • US 4,460,734 describes a polymer composition
  • a polyalkoxylated linear aliphatic alcohol as leveling agent and a polymer, usually in form of a water insoluble latex polymer prepared by emulsion polymerisation and dispersed in the aqueous medium.
  • This polymer compo- sition may be used to formulate aqueous polishes, in particular aqueous floor polishes.
  • the linear aliphatic alcohol is polyalkoxylated with at least one compound selected from the group consisting of ethylene oxide, propylene oxide and epichlorohydrin.
  • the leveling agent is at least one compound selected from the group consisting of polyalkoxylated linear alcohols of formula CH3(CH2)mO(CH2CH20) n H, wherein m and n are integers and n is greater than one.
  • m is an integer from 9 to 15, and n is an integer from 2 to 6.
  • the leveling agent may be composed of mixtures of polyalkoxylated linear aliphatic alcohols.
  • the average value of m is about 12.5 and the average value of n is from 2 to 4. It is more preferable that the average value of n is 3.
  • Examples 5, 6 and 7 describe the performance of aqueous floor polishes comprising polyethoxylated linear aliphatic alcohols.
  • Comparative example 3 describes the performance of aqueous floor polishes comprising Triton® X-45, which is ethoxylated octylphenol, having an average number ethylene oxide units of 7 to 8.
  • JP 6-080933 describes a floor polish composition comprising a polymer, a wax and an adipic ester.
  • JP 2004-107586 describes a floor polish composition containing (i) R a -0-(PO)m-(EO) n -H (I) or Rb-C6H4-0-(PO)m-(EO)n-H (II), wherein R a and Rb denote alkenyl or linear or branched alkyl group of 6 to 22 carbon atoms, PO represents a propylenoxide unit, EO represents an ethylene oxide unit, m is 0 to 3 and n is 1 to 8, and (ii) one or more kinds of compounds of formulae (1 ) to (8).
  • US 7,378,381 B2 describes floor coating compositions comprising a C7-10 aliphatic monocarbox- ylic acid monoester of a diol, or 2) a C7-10 aliphatic monocarboxylic acid monoester or diester of a triol.
  • R a is Ce-30-alkyl
  • L a is C2-6-alkylene
  • n is an integer from 1 to 10
  • R b is Ci-io-alkyl
  • L b is C2-6-alkylene
  • n 1 to 12
  • o is an integer from 1 to 5.
  • Ci-3-alkyl, Ci-5-alkyl, Ci-10-alkyl, Cio-is-alkyl, Cs-2o-alkyl and C6-3o-alkyl can be branched or un- branched.
  • Examples of Ci-3-alkyl are methyl, n-ethyl, n-propy and isopropyl. Examples of
  • Ci-5-alkyl are Ci-3-alkyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl and isopentyl.
  • Examples of Ci-io-alkyl are Ci-5-alkyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, 1 ,1 -dimethyl-3,3-dimethyl- butyl, n-nonyl and n-decyl.
  • Cio-15-alkyl examples are n-decyl, n-undecyl, n-dodecyl, n-tridecyl, iso-tridecyl, n-tetradecyl and n-pentadecyl.
  • Examples of Cs-2o-alkyl are n-octyl, 2-ethylhexyl, 1 ,1 -dimethyl-3,3-dimethylbutyl, n-nonyl, Cio-is-alkyl, hexadecyl, heptadecyl, octadecyl, non- adecyl and eicosyl.
  • C6-3o-alkyl examples include n-hexyl, n-heptyl, Cs-2o-alkyl, n-docosyl, n-tetracosyl, n-hexacosyl, n-octacosyl and n-triacontyl.
  • C2-3-alkylene and C2-6-alkylene can be branched or unbranched.
  • Examples of C2-3-alkylene are ethylene, propylene and (l -methyl)ethylene.
  • Examples of C2-6-alkylene are C2-3-alkylene and butylene, (l -methyl)propylene, (2-methyl)propylene, pentylene and hexylene.
  • R a is C 8 -2o-alkyl.
  • R a is Cio-is-alkyl.
  • R a is n-decyl, n-dodecyl, n- tridecyl, iso- tridecyl, n-tetradecyln or n-pentadecyl.
  • L a is C2-3-alkylene.
  • L a is ethylene.
  • n is an integer from 1 to 5.
  • n is an integer from 2 to 4.
  • R b is Ci -5 -alkyl.
  • R b is Ci-3-alkyl.
  • R b is methyl
  • L b is C2-3-alkylene.
  • L b is C3-alkylene.
  • L b is (l -methyl)ethylene.
  • n is an integer from 2 to 10.
  • n is an integer from 4 to 8.
  • o is 1 or 2.
  • Preferred blends contain i) a compound of formula mixture of compounds of formula (A), wherein
  • R a is Cs-20-alkyl
  • L a is C2-3-alkylene
  • n is an integer from 1 to 5, and ii) a compound formula
  • R b is Ci-5-alkyl
  • L b is C2-3-alkylene
  • n is an integer from 2 to 10
  • o is an integer from 1 to 2.
  • More preferred blends contain i) a compound of formula
  • R a is Cio-15-alkyl
  • L a is ethylene
  • n is an integer from 2 to 4, and ii) a compound formula
  • R b is Ci-3-alkyl
  • L b is C3-alkylene
  • n is an integer from 4 to 8, and o is 1 .
  • Most preferred blends contain i) a compound of formula mixture of compounds of formula (A), wherein R a is n-decyl, n-dodecyl, n- tridecyl, iso- tridecyl, n-tetradecyln or n-pentadecyl, L a is ethylene, and
  • n 2 to 4
  • R b is methyl
  • L b is (l -methy)ethylene
  • n 4 to 8
  • o 1 .
  • (A)/compounds of formula (B) or mixtures of compounds of formula (B) is preferably 20/80 to 80/20, more preferably 30/70 to 70/30, even more preferably 40/60 to 60/40 and most preferably 45/55 to 55/45.
  • the compounds of formula (A) and the compounds of formula (B) are commercially available or can be prepared by methods known in the art.
  • the blends can be prepared by mixing the compound of formula (A) or mixtures of compounds of formula (A) with compounds of formula (B) or mixtures of compounds of formula (B), preferably at a temperature in the range of 25 to 50 °C.
  • the floor coating compositions comprising the inventive blends.
  • the floor coating compositions usually comprise 0.01 to 10%, preferably 0.5 to 5%, more preferably 1 to 4%, by weight of the blends of the present invention based on the weight of the floor coating composition.
  • the floor coating composition may comprise additional ingredients such as polymers, waxes, surfactants, anti-foam agents, mineral oils, preservatives and fragrances.
  • polymers are acrylic polymers.
  • waxes are polypropylene-maleic anhydride graft polymers and oxidized polyethylene polymers.
  • surfactants are fluoro- surfactants.
  • a preservatives are benzoisothiazolinon and mixtures of methylisothi- azolinon and chloroisothiazolin.
  • the coating composition comprises the blends of the present invention, polymers, waxes, surfactants, anti-foam agents and preservatives. It is preferred that the coating composi- tion does not comprise alkali soluble resins.
  • the dry mass ratio of polymer/wax is usually between 99/1 to 50/50, preferably between 95/5 to 70/30, more preferably between 90/10 to 85/15.
  • the pH of the floor coating composition is usually in the range of 8 to 9.
  • the coating composition may be prepared by mixing the blend of the present invention with the additional ingredients of the coating composition, preferably at a temperature in the range of 25 to 50 °C. After the mixing, the pH of the coating composition may be adjusted, for example using ammonium hydroxide solution.
  • blends of the present invention as leveling, plasticizing and water-spot resistance agents in floor coating compositions.
  • the blends of the present invention show a well-balanced combination of leveling properties, plasticizing properties and water-spot resistance properties.
  • inventive blends 1 to 5 all show at the same time a leveling of at least 4 as de- termined by ASTM D3153-87, a Pencil Hardness of at least 3H as determined by ASTM D3363- 05, a Pendulum Hardness of maximum 32 as determined by DIN EN 1522 (2007) a water-spot resistance of at least 4 as determined by ASTM D1793-92.
  • the amount of the compounds A and compounds B of the blend are given in weight percent based on the weight of the blend.
  • antifoam agent blend of mineral oil, emul- 100 0.06
  • Table 3 The solid content is given in weight percent based on the weight of the ingredient. 2 The amount of the ingredients is given in weight percent based on the weight of the floor coating formulation. 3 TBEP is tributoxyethyl phosphate. 4 The floor coating formulation comprising the blends of example 2 or TBEP are comparative floor coating formulations.
  • the pH of the floor coating formulation is adjusted to pH 8-9 using ammonium hydroxide solution (25%).
  • the floor coating formulations of example 3 are evaluated on black PVC composite tiles, 0.09 m 2 , produced by Fademac.
  • the application rate of the floor coating formulations is 33.3 g/m 2 , equivalent to 3 ml. of the floor coating formulations applied over the tile per coat
  • the applied floor coating formulations show the following performance.
  • Blend 1 Blend 2 Blend 3 Blend 4 Blend 5
  • Pencil Hardness and the Pendulum Hardness describe the plasticizing properties of an additive. The higher the Pencil Hardness and the lower the Pendulum Hardness, the better are the plasticizing properties.
  • Table 4 shows that the inventive blends 1 to 5 all show at the same time good leveling properties, good plasticizing properties and good water-spot resistance properties.
  • the inventive blends 1 to 5 all show at the same time a leveling of at least 4 as determined by ASTM D3153-87, a Pencil Hardness of at least 3H as determined by ASTM D3363-05, a Pendulum Hardness of maximum 32 as determined by DIN EN 1522 (2007) and a water-spot resistance of at least 4 as determined by ASTM D1793-92.
  • the comparative additive tributoxyethyl phosphate shows a high leveling of 4 to 5, and a good water-spot resistance of 4, but the plasticizing properties are very poor.
  • the Pencil Hardness is 2H and the Pendulum Hardness is 36.
  • the comparative blends 1 and 2 comprising at least one compound of formula A, but no compound of formula B show a good leveling of 4, but the water-spot resistance is only 3 to 4, and the Pencil Hardness of comparative blend 1 is only 2H.
  • the comparative blends 3 and 4 comprising at least one compound of formula B, but no com- pound of formula A show high plasticizing properties, but a poor leveling of 3, respectively, 3 to 4, and a poor water-spot resistance of 3 to 4.
  • inventive blends of the present invention show well-balanced leveling, plasticizing and water-spot resistance properties.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne des mélanges contenant : i) un composé de formule (A) ou un mélange de composés de formule (A), dans laquelle Ra représente C6-30-alkyle, La repésente C2-6-alkylène et n est un nombre entier de 1 à 10 ; et ii) un composé de formule (B) ou un mélange de composés de formule (B), dans laquelle Rb rerpésente C1-10-alkyle, Lb représente C2-6-alkylène, m est un nombre entier de 1 à 12 et o est un entier de 1 à 5. L'invention concerne également des compositions de revêtement de sol contenant ces mélanges.
PCT/EP2015/060345 2014-05-23 2015-05-11 Additif polyvalent pour préparation de revêtement de sol Ceased WO2015176984A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP14169554 2014-05-23
EP14169554.4 2014-05-23

Publications (1)

Publication Number Publication Date
WO2015176984A1 true WO2015176984A1 (fr) 2015-11-26

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ID=50771160

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Application Number Title Priority Date Filing Date
PCT/EP2015/060345 Ceased WO2015176984A1 (fr) 2014-05-23 2015-05-11 Additif polyvalent pour préparation de revêtement de sol

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH464413A (de) * 1964-10-19 1968-10-31 Staley Mfg Co A E Saures Überzugsmittel, insbesondere Bodenpflegemittel
US20110233461A1 (en) * 2008-10-14 2011-09-29 Gunther Wasow Method for minimizing the diameter of a urea solution, urea solution and use of a surfactant in urea solution

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH464413A (de) * 1964-10-19 1968-10-31 Staley Mfg Co A E Saures Überzugsmittel, insbesondere Bodenpflegemittel
US20110233461A1 (en) * 2008-10-14 2011-09-29 Gunther Wasow Method for minimizing the diameter of a urea solution, urea solution and use of a surfactant in urea solution

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